Five times Chuck Bass falls in love
by endless blue skies
Summary: The five times Chuck Bass falls in love with Blair Waldorf.  Because contrary to popular belief, the first time Chuck Bass fell in love with Blair Waldorf was not at the back of his limo or in his beloved Victrola. ONESHOT


Five times Chuck Bass falls in love with Blair Waldorf.

Contrary to popular belief, the first time Chuck Bass fell in love with Blair Waldorf was not at the back of his sacred limo or in his beloved Victrola.

Flashback to six years old on that summer day in the van der Bilt home in the Hamptons, before Nate and Blair, before always have and always will. To the days when he thought girls didn't matter and matchbox cars were the shit. On that day when he and Nate pretended to be X-men. (He was Cyclops ofcourse, Cyclops got to wear awesome sunglasses and Chuck always thought sunglasses made you a billion times cooler.)

When he first saw the brunette who was sitting with her tiny legs crossed as she ate an ice cream cone.

Running towards her, he flashed her a smirk and placed his hands on his hips. (Nate wouldn't find him, Nate was _Wolverine_, plus he was awful at hide and seek X-men style.) "I'm Chuck Bass." Were the first three words he told her.

"I'm gonna melt your ice cream!"

"You can't do that! My _daddy_ bought me this ice cream cone!" she pouted, looking at him angrily.

And Chuck frowned. No girl was allowed to tell him what to do and what he couldn't do. So he shot her a glare and took off his sunglasses as he pushed the ice cream out of her dainty fingers and unto the grass.

"You're a stupid boy! I'm telling my daddy!" the brunette cried, Chuck kept his hands behind his back and smirked.

He always won.

"If you tell, i'm telling everyone else you got cooties." he smirked. She wiped her tears from her eyes and shoved him hard enough to make him lose balance and fall on the ground and in that moment he saw her differently. She was different, she didn't run away and cry and she fought and he liked that. (He didn't! _He didn't._ Girls were stupid and dumb.)

"'I don't have cooties!" she yelled, stepped over his chest with her stupid girl shoes. (And he likes it because no girl has ever had the guts to fight Chuck Bass. Maybe it was love.)

"Chuck! Chuck! Are you okay?" Nate asked, running towards him. "Oh, hey Blair. What happened to Chuck?"

He watched her blush at the sight of the blonde boy. "He fell and I wanted to help him." she smiled, getting off Chuck. "But I dropped my ice cream and my _daddy_ got me that ice cream."

"Let's get more ice cream inside, Grandpa has a big fridge full of ice cream sundaes!" Nate exclaimed, taking her hand. "Let's go inside."

"What about me?" Chuck frowned, sitting up. He wanted Blair to hold his hand too. "I don't want ice cream."

"You can play by yourself first. Me and Blair will get ice cream first." Nate smiled as they ran into the kitchen.

And from that moment on, Chuck swore there was no happily ever after.

* * *

Then they were in seventh grade before St. Jude's and Constance Billard.

The brunette was at the top of her class and she held her head high and it was a stupid cliche. (Home economics partners.) "You put two eggs in this." She directed as she read the ingredients for cookies, he glared because fucking hell, he didn't care about cookies or the stupid brunette (who was now already dating his best friend.) or his grades. (Bart wouldn't care either, Bart _never_ cared.)

He put flour in the batter instead.

"Eggs, Chuck! Do you want us to _fail_?" she exclaimed, looking around the classroom. The whole class was buzzing about uncontrollably, looking confused and ready to drop out the stupid class that trained them how to be fucking housewives.

"I don't care." were the first three words he told her that day.

"That's just the problem, you never care. No wonder Nate never hangs out with you anymore." she shot at him.

He frowned as he tossed some flour towards her face. "Nate never hangs out with me because you're always in the fucking way with your stupid _Tiffany's_ tradition and picnics!"

And it hit her hard like a slap. "It's not stupid!" she grinded her teeth and wiped the flour off her face.

"That's right, _you_ are." With her ridiculous girl parties and croissants and kisses and holding hands. (Maybe he wanted her to hold his hand instead.)

A knee against his groin shot pain through his whole body. "I hate you so much."

"What's...new?" he groaned, leaning agaisnt the table. "You never...even...liked me."

"You're Chuck Bass." she spat as if it were venom. As if his name was poison on her tongue. "Who even likes you?"

The stared at her for a moment and tossed an egg towards her, hitting her on the nose exactly because what she said has hurt more than a punch in the face because it was true. It was real. Who liked-let alone_ loved_ him? Bart had made it clear to him that he was unwanted, Nate had been ditching him for Blair and Serena was always out with Georgina. So who was he left with? Who was left to love Chuck Bass? No one. "You're stupid." The brunette wiped her face as he stormed out.

What was love?

Holding hands and having dinner, kissing in public and watching movies. Hugging and doing homework together. Good luck charms and butterflies.

He thought about it for a long time as he stood in the courtyard, head low with his hands behind his back as he leaned on the wall sideways and he decided to fuck it all and forget love because love was mythic, a sad philosophy idiots like Blair Waldorf believed in. Just when he decided that love didn't matter, the brunette came rushing towards him as she breathed in and out heavily.

"What are you doing here, Waldorf?"

"What you did to me in there was immature, Bass." she mumbled, sitting on a bench next to him. "But I didn't mean it when I said nobody liked you."

He stared down at her. "Say what you mean."

"I didn't mean it. I like you _sometimes_ and Serena does too when she's not out partying and even Nate because he's your best friend."

_I like you sometimes._

"You're an awful liar, Waldorf. Like I said back inside, when have you ever liked me?" he muttered as Blair stood up and walked towards him.

"Look Chuck, this will probably be the only time i'll ever admit it but you're my friend and I care because i've known you since we were nine-" _six_. "and I can't lose you even if I wanted to." she smiled, placing her hand on his cheek.

He closed his eyes and breathed out. "I'm not your property." Because she can't own him like her minions and because he wanted to be more to her than just another person she owned and destroyed.

"You're more than that, Chuck." she whispered, her breath on his face and then it was her lips on his.

They always said third time's the charm and maybe it was.

"Are you sure?" Were the three words that came out of him as the brunette pressed her lips agaisnt his.

And at the back of the limo, it happened. To him, to her and to the nonexistent heart that beat in his chest. It happened and that was when the butterflies came and never left.

* * *

The fourth time was in Europe. Around the world, away from Manhattan, away from the brunette. Inside a random hotel room with a random French girl whose name slipped his mind because he was too high to remember.

And it was until he saw familiar black stockings sprawled across the floor when he remembered her and he swore he saw her looking at him with a disappointed expression on her face. '_Pick it up_' Ghost Blair said. '_Three words, eight letters._'

"_Monsieur, revenez au lit_." One of the French girls begged as he looked out the window.

"_Dans un deuxieme dames_." he muttered, closing his eyes. He wanted to know if what he did was right. If leaving the brunette did him right because he couldn't risk falling in love deeper. _He didn't need love_. He was Chuck Bass.

But the stockings laid there, taunting him.

Home is where the heart is. (Blair Waldorf had his heart from the beginning.) So he ran out because of love and fairytales and because it was all worth it for the brunette.

* * *

The fifth time was in the train station in Paris. When she handed him the diamond ring and smiled.

"I destroyed the only thing I ever loved." _I love you_ rolls along his tongue and it was over used because it was like nothing to them anymore but it brought him back. 3 words, 8 letters. A year ago. Back when it was love and the two of them.

"I don't love you anymore but... it takes more than that to destroy a Waldorf." she said and he could do nothing but swallow the _I love you_.

He left even more broken than he was before but decided to come back and start over. New York with Eva wouldn't be bad.

**Well, this sucks but i've been wanting to write one of those five things prompts and this idea just came into my mind during one of my Algebra classes. So, here I am. I'm not exactly happy since i'm not really good at Chuck-centric shit but I hope you guys enjoyed. Reviews are as lovely as Daddy!Dan and BB Milo. :)**

**OH, PS. Check out my other fic. Maybe, Tonight. It's D/B tho but idk. Maybe you guys would like it.**


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